INTRAMOLECULAR ADDITION OF VINYL RADICALS TO ALDEHYDES

Authors
DEVIN P FENSTERBANK L MALACRIA M
Citation
P. Devin et al., INTRAMOLECULAR ADDITION OF VINYL RADICALS TO ALDEHYDES, Tetrahedron letters, 39(8), 1998, pp. 833-836
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
8
Year of publication
1998
Pages
833 - 836
Database
ISI
SICI code
0040-4039(1998)39:8<833:IAOVRT>2.0.ZU;2-F
Abstract
The reaction of aldehydes 1 and 10 with Bu3SnH has been studied. In th ermal conditions, after an initial chemoselective 6-exo-trig or 5-exo- trig cyclization to the aldehyde, a beta-scission reaction takes place , providing rearrangement products. At low temperature, using the Et3B /O-2 procedure, satisfactory yields of cyclohexanol 2 and cyclopentano l 11 are obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.